Carbon tetrabromide → HCID 68632463, compound

HRID 1799449Notes

Reaction equation

HRID 1799449 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29]O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:32].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:32][CH2:29][CH2:28][O:27][CH2:26][CH2:25][O:24][CH2:23][CH2:22][O:21][CH2:20][CH2:19][O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 59408054HCID 59408054, compound

Product 1

HCID 68632463HCID 68632463, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Compound 10 (651 mg, 1.50 mmol) and carbon tetrabromide (628 mg, 1.88 mmol) were dissolved in tetrahydrofuran (THF, 0.5 mL). Triphenylphosphine (498 mg, 1.88 mmol) was added to this solution portionwise over 5 min with stirring and additional amount of THF (0.5 mL) was added to the mixture. Reaction was monitored by TLC, which indicated that it was over in 10 min Solvent was removed at room temperature and the crude product was chromatographed (SiO2, hexane/EtOAc 2:1) to give 767 mg (1.55 mmol, >100%, less dry) of 35 as a clear colorless oil. Rf 0.74 (hexane/EtOAc 1:1); 1H NMR (400 MHz, CDCl3) 7.68 (m, 4H, H-2 of phenyl), 7.45-7.35 (m, 6H, H-3 and H-4 of phenyl), 3.81 (t, 2H, J=5.5 Hz, CH2CH2OSi), 3.79 (t, 2H, J=7.1 Hz, CH2CH2Br), 3.65 (m, 8H, (OCH2CH2)2OCH2CH2OSi), 3.61 (t, 2H, J=5.3 Hz, CH2CH2OSi), 3.45 (t, 2H, J=6.4 Hz, CH2CH2Br), 1.05 (s, 9H, C(CH3)3); MS (ESI) Calcd for C24H35BrO4SiNa (M+Na+): 517.1. Found: 517.1.

Workup

  1. customReaction
  2. customwas over in 10 min Solvent
  3. customwas removed at room temperature
  4. customthe crude product was chromatographed (SiO2, hexane/EtOAc 2:1)
  5. customto give 767 mg (1.55 mmol, >100%
  6. dry with materialless dry) of 35 as a clear colorless oil

Sources & evidence

ORD record
ord-13d9858763ff4929b59904d390f44796
Source dataset
uspto-grants-2013_01
Patent number
US08344125B2

Reaction notes

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